Vacation Rentals with Pool in The Oaks Club, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Sarasota
  6.  The Oaks Club

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2369 Best Vacation Rentals with Pool in The Oaks Club (Starting from $60)

Windsor Lodge Unit 20, studio, 1BR 1BA close to the beaches, pool access
Windsor Lodge Unit 20, studio, 1BR 1BA close to the beaches, pool access
Apartment
Osprey, FL, USA
0.7k from The Oaks Club center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$176
Average price / night
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Furnished and meticulous!  Near Nokomis, Venice and Siesta Beaches.
Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches.
Condo
Osprey, FL, 34229, United States
0.6k from The Oaks Club center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$249
Average price / night
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Windsor Lodge Unit 3 close to the Beaches Siesta Key
Windsor Lodge Unit 3 close to the Beaches Siesta Key
Apartment
Osprey, FL, USA
0.7k from The Oaks Club center

Apartments, Accommodations, Pools, Parking, Cabins, Lodgings, Places to stay, Family, Self-catering

1 Bedroom4 Guests
9.0

Fabulous

1 reviews

$206
Average price / night
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Windsor Lodge Unit 15, studio, close to the beaches, pool access
Windsor Lodge Unit 15, studio, close to the beaches, pool access
Apartment
Osprey, FL, 34229, United States
0.7k from The Oaks Club center

AC, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
9.2

Superb

5 reviews

$222
Average price / night
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Windsor Lodge Unit #19, studio close to beaches
Windsor Lodge Unit #19, studio close to beaches
Apartment
Osprey, FL, USA
0.7k from The Oaks Club center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$223
Average price / night
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Windsor Lodge Unit 7, studio, close to the beaches, pool access
Windsor Lodge Unit 7, studio, close to the beaches, pool access
Apartment
Osprey, FL, 34229, United States
0.9k from The Oaks Club center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Pool, Washer

1 Bedroom4 Guests
9.4

Superb

3 reviews

$216
Average price / night
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Pool, Hot tub, Close to Beaches, Shopping, More!
Pool, Hot tub, Close to Beaches, Shopping, More!
House
The Oaks Club, Osprey, Florida, USA
1.3k from The Oaks Club center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Jacuzzis

3 Bedrooms8 Guests
New to Booking
$425
Average price / night
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2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view!
2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view!
Condo
Osprey, FL, 34229, United States
1.0k from The Oaks Club center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$193
Average price / night
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Florida Vacation Condo
Florida Vacation Condo
Apartment
Sarasota, FL, USA
2.9k from The Oaks Club center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Hot tubs, Places to stay

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$60
Average price / night
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Charming 3-bedroom condo with WiFi, AC in tranquil Osprey
Charming 3-bedroom condo with WiFi, AC in tranquil Osprey
Condo
Osprey, FL, 34229, United States
1.1k from The Oaks Club center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$244
Average price / night
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Sarasota - Dunmore 8730
Sarasota - Dunmore 8730
House
Sarasota, FL, USA
3.1k from The Oaks Club center

Guest Services, Security/Safety, Pool, Barbecue/Outdoor Cooking, Child Friendly

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$180
Average price / night
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Pet Friendly Paradise  Close To Sarasota-Venice
Pet Friendly Paradise Close To Sarasota-Venice
House
Osprey, FL, 34229, United States
1.2k from The Oaks Club center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms5 Guests
9.8

Exceptional

59 reviews

$259
Average price / night
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Turtle Bay Beauty
Turtle Bay Beauty
Apartment
Sarasota, FL, USA
3.4k from The Oaks Club center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay, Accessible hotels

2 Bedrooms4 Guests
New to Booking
$194
Average price / night
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Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock
Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock
House
Osprey, FL, 34229, United States
1.2k from The Oaks Club center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

12 reviews

$298
Average price / night
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Turtle Beach Resort
Turtle Beach Resort
Resort
Siesta Key, FL, USA
3.5k from The Oaks Club center

Accommodations, Pools, Resorts, Parking, Pet-friendly, 4-star, Lodgings, Hot tubs, Places to stay

20 Bedrooms44 Guests
9.0

Fabulous

77 reviews

$454
Average price / night
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Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
House
Osprey, FL, 34229, United States
1.4k from The Oaks Club center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
8.8

Fabulous

28 reviews

$269
Average price / night
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The Sea Side Villa
The Sea Side Villa
House
Sarasota, FL, USA
3.5k from The Oaks Club center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms4 Guests
New to Booking
$237
Average price / night
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Immaculate, quiet, pet and family-friendly pool home backing on pond
Immaculate, quiet, pet and family-friendly pool home backing on pond
House
Sarasota, FL, 34238, United States
1.4k from The Oaks Club center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$119
Average price / night
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Bayside Escape-Condo w Dock Pool and Near Beach
Bayside Escape-Condo w Dock Pool and Near Beach
House
Sarasota, FL, USA
3.6k from The Oaks Club center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$373
Average price / night
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Beautiful home on an 18 holes golf course
Beautiful home on an 18 holes golf course
House
Sarasota, FL, 34238, United States
1.7k from The Oaks Club center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$500
Average price / night
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Manatee Key-Waterfront Minutes to Turtle Beach
Manatee Key-Waterfront Minutes to Turtle Beach
Apartment
Sarasota, FL, USA
3.6k from The Oaks Club center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$363
Average price / night
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Paradise Home away from Home: Golf, Swimming, Tennis, & lots of Fun in the Sun!
Paradise Home away from Home: Golf, Swimming, Tennis, & lots of Fun in the Sun!
Condo
Sarasota, FL, 34238, United States
1.7k from The Oaks Club center

AC, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
9.4

Superb

18 reviews

$202
Average price / night
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Homey Comfort Meets Championship Golf–Ground Floor Condo in Stoneybrook Sarasota
Homey Comfort Meets Championship Golf–Ground Floor Condo in Stoneybrook Sarasota
Condo
Sarasota, FL, 34238, United States
1.8k from The Oaks Club center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Laundry, Living Area

2 Bedrooms6 Guests
New to Booking
$228
Average price / night
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2BR/2BA 1st Floor Condo in Stoneybrook Golf & Country Club
2BR/2BA 1st Floor Condo in Stoneybrook Golf & Country Club
Condo
Sarasota, FL, 34238, United States
1.8k from The Oaks Club center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms4 Guests
10.0

Exceptional

12 reviews

$109
Average price / night
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Completely Renovated 2 BR + Den condo @ Stoneybrook CC
Completely Renovated 2 BR + Den condo @ Stoneybrook CC
Condo
Sarasota, FL, 34238, United States
1.9k from The Oaks Club center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$113
Average price / night
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Enjoy this Condo Hideaway Casey Key area of Sarasota Relax and Enjoy this Secret
Enjoy this Condo Hideaway Casey Key area of Sarasota Relax and Enjoy this Secret
Condo
Osprey, FL, 34229, United States
2.0k from The Oaks Club center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
New to Booking
$146
Average price / night
Check Availability
Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis
Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis
Condo
Osprey, FL, 34229, United States
2.1k from The Oaks Club center

AC, Balcony, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$136
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in The Oaks Club.

Where to stay in The Oaks Club? Best neighborhoods & areas

The Oaks Club Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 2369 verified vacation rentals with a pool in The Oaks Club. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in The Oaks Club vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $60 per night, with private pool homes and peak travel periods often costing more.

Many rentals in The Oaks Club offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in The Oaks Club welcome pets. Currently, 42 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in The Oaks Club often include additional outdoor features such as Pool, Fireplace/Heating, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in The Oaks Club offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.